— 97 — 



When the original oil was treated with highly-diluted soda liquor 

 it proved to contain an oily acid of a high b. p. as well as traces 

 of a phenol. In order to separate these two the oil, after being 

 recovered from the soda liquor, was treated with carbonate of soda 

 solution. The acid which had separated from the carbonate solution on 

 acidulation may , however, not be a uniform one, as might be concluded 

 from its b. p. and its behaviour as detailed below. Apart from an 

 unimportant first runnings (b. p. 115 to 125 , 5 — 6 mm. press.) it 

 boiled at 125 to 13 1°. Its other constants were as follows: b. p. 257 

 to 263 at normal press., d 15 o 0,9394, « D + 5 2', n D20O 1,45611. 

 These properties, and the silver content as ascertained by analysis of 

 its silver salt recrystallised from water, indicate citronellic acid 



C10 His O2 : 



0,3079 sbst. : 0,1196 g. Ag. 



Found : Calc. for C 10 H 17 Ag0 2 : 



Ag 38,84% 38,77% 



In order to identify the acid more closely recourse was had to the 



amide of citronellic acid, m. p. 81 to 8 2°. For its preparation, the 



acid was first converted into the chloride (b. p. 122 to 125 , 6 mm.) 



by means of thionyl chloride, and the latter converted into the amide 



with aqueous ammonia. The amide purified from petroleum ether 



melted not quite sharply at 87 to 88°, that is to say, 6° higher 



than that obtained by Tiemann 1 ) from citronellic acid nitrile. It 



is our intention, for purposes of comparison, to prepare the amide 



of synthetic citronellic acid, in order to determine by this means 



whether the above-mentioned acid really represents citronellic acid 



(the existence of which in essential oils has not been detected up to 



the present), or another acid of the same constitution. In addition 



to the arguments adduced above, its identity with citronellic acid 



seems to be indicated by the fact that the oil contains both citronellol 



and citronellal. 



Only traces of the phenol referred to above were at our disposal. 



These were just sufficient to enable us to identify it by its benzoyl 



combination. This body, obtained by Schotten-Baumann's method, 



when purified from petroleum ether, had a m. p. of 109 to 1 io°, but up 



to the present we have been unable to identify it with the benzoate 



of any known phenol. 



From the Instituto Medico Nacional in Mexico we received the 

 two following distillates: — 



Oil of Satureja macrostema (Benth.) Briq. (Calamintha 

 macrostema Benth.). The oil of this shrub-like plant, which belongs to 



*) Berl. Berichte 31 (1898), 2899. 



